Copper-Catalyzed gem-Difluoroolefination of Diazo Compounds with TMSCF3 via C-F Bond Cleavage

被引:203
|
作者
Hu, Mingyou [1 ]
He, Zhengbiao [1 ]
Gao, Bing [1 ]
Li, Lingchun [1 ]
Ni, Chuanfa [1 ]
Hu, Jinbo [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
CROSS-COUPLING REACTIONS; 1,1-DIFLUORO OLEFINS; H BOND; CARBONYL-COMPOUNDS; CONVENIENT METHOD; METAL CARBENE; TRIFLUOROMETHYLATION; FLUORINATION; ACTIVATION; CONVERSION;
D O I
10.1021/ja409941r
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel Cu-catalyzed gem-difluoroolefination of diazo compounds is described. This transformation starts from readily available TMSCF3 and diazo compounds, via trifluoromethylation followed by C-F bond cleavage, to afford the desired 1,1-difluoroalkene products.
引用
收藏
页码:17302 / 17305
页数:4
相关论文
共 50 条
  • [1] Copper-catalyzed gem -difluoroolefination of diazo compounds with TMSCF3 via C-F bond cleavage
    Hu, J. (jinbohu@sioc.ac.cn), 1600, American Chemical Society (135):
  • [2] gem-Difluoroolefination of Diazo Compounds with TMSCF3 or TMSCF2Br: Transition-Metal-Free Cross-Coupling of Two Carbene Precursors
    Hu, Mingyou
    Ni, Chuanfa
    Li, Lingchun
    Han, Yongxin
    Hu, Jinbo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (45) : 14496 - 14501
  • [3] Use of TMSCF 3 for gem-difluoroolefination of carbonyl compounds: The right conditions
    Krishnamoorthy, Sankarganesh
    Kothandaraman, Jotheeswari
    Saldana, Jacqueline
    Prakash, Surya
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [4] From C1 to C3: Copper-Catalyzed gem-Bis(trifluoromethyl)olefination of α-Diazo Esters with TMSCF3
    Wang, Qian
    Ni, Chuanfa
    Hu, Mingyou
    Xie, Qiqiang
    Liu, Qinghe
    Pan, Shitao
    Hu, Jinbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (22) : 8507 - 8511
  • [5] From C1 to C3 : Copper-Catalyzed gem-Bis(trifluoromethyl)olefination of α-Diazo Esters with TMSCF3
    Wang, Qian
    Ni, Chuanfa
    Hu, Mingyou
    Xie, Qiqiang
    Liu, Qinghe
    Pan, Shitao
    Hu, Jinbo
    Advanced Materials, 2020, 132 (22) : 8585 - 8589
  • [6] Copper-catalyzed α-selective C–H trifluoromethylation of acrylamides with TMSCF3
    Shang-Zheng Sun
    Hui Xu
    Hui-Xiong Dai
    Chinese Chemical Letters, 2019, 30 (05) : 969 - 972
  • [7] Copper-catalyzed α-selective C-H trifluoromethylation of acrylamides with TMSCF3
    Sun, Shang-Zheng
    Xu, Hui
    Dai, Hui-Xiong
    CHINESE CHEMICAL LETTERS, 2019, 30 (05) : 969 - 972
  • [8] Copper-Catalyzed Oxidative Trifluoromethylthiolation of Aryl Boronic Acids with TMSCF3 and Elemental Sulfur
    Chen, Chao
    Xie, Yan
    Chu, Lingling
    Wang, Ruo-Wen
    Zhang, Xingang
    Qing, Feng-Ling
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (10) : 2492 - 2495
  • [9] Synthesis of gem-Difluoroalkenes via Nickel-Catalyzed Reductive C-F and C-O Bond Cleavage
    Lin, Zhiyang
    Lan, Yun
    Wang, Chuan
    ACS CATALYSIS, 2019, 9 (01) : 775 - 780
  • [10] Advances in silylation and borylation of fluoroarenes and gem-difluoroalkenes via C-F bond cleavage
    Zhang, Juan
    Geng, Shasha
    Feng, Zhang
    CHEMICAL COMMUNICATIONS, 2021, 57 (90) : 11922 - 11934